2,6-Diformylpyridine Explained

2,6-Diformylpyridine is an organic compound with the formula C₅H₃N(CHO)₂, and typically appears as a solid powder at room temperature. The molecule features formyl groups adjacent to the nitrogen of pyridine. The compound is prepared by oxidation of 2,6-dimethylpyridine.^[1]

It condenses with amines to give diiminopyridine ligands,^[2] as was demonstrated in Fraser Stoddart's synthesis of molecular Borromean rings.^{[3] [4] [5]} It also finds use in the preparation of metal-coordinated polymer materials.^{[6] [7]}

Related compounds

• 2,6-Diacetylpyridine
• Isophthalaldehyde

Notes and References

1. 10.1016/S0166-9834(00)82465-3. Vapour Phase Oxidation of 2,6-Lutidine to 2,6-Pyridinedicarboxaldehyde. III: Kinetic Study. 1987. Forni. Lucio. Casalone. Gianluigi. Applied Catalysis. 34. 317–328.
2. 10.1021/ja990449w. Iron and Cobalt Ethylene Polymerization Catalysts Bearing 2,6-Bis(Imino)Pyridyl Ligands: Synthesis, Structures, and Polymerization Studies. 1999. Britovsek. George J. P.. Bruce. Michael. Gibson. Vernon C.. Kimberley. Brian S.. Maddox. Peter J.. Mastroianni. Sergio. McTavish. Stuart J.. Redshaw. Carl. Solan. Gregory A.. Strömberg. Staffan. White. Andrew J. P.. Williams. David J.. Journal of the American Chemical Society. 121. 38. 8728–8740.
3. 10.1126/science.1096914. Molecular Borromean Rings. 2004. Chichak. K. S.. Cantrill. S. J.. Pease. A. R.. Chiu. S.-H.. Cave. G. W. V.. Atwood. J. L.. Stoddart. J. F.. James Fraser Stoddart. . 304. 5675. 1308–1312. 15166376. 2004Sci...304.1308C. 45191675.
4. 10.1039/B505730B. Nanoscale Borromean links for real. 2005. Peters. Andrea J.. Chichak. Kelly S.. Cantrill. Stuart J.. Stoddart. J. Fraser. James Fraser Stoddart. Chemical Communications. 27. 3394–6. 15997275.
5. Book: 188. Historical Perspective on the Discovery of Covalent Organic Frameworks. https://books.google.com/books?id=06iODwAAQBAJ&pg=PA188. Introduction to Reticular Chemistry: Metal-Organic Frameworks and Covalent Organic Frameworks. Omar M.. Yaghi. Omar M. Yaghi. Markus J.. Kalmutzki. Christian S. . Diercks. Wiley-VCH. 2019. 9783527821082.
6. 10.1002/marc.202200790 . Metal Coordination in Polyimine Covalent Adaptable Networks for Tunable Material Properties and Enhanced Creep Resistance . Sybren K. . Schoustra . Maarten M. J. . Smulders . Macromolecular Rapid Communications . 2023 . 44 . 5 . 2200790. 36629864 . 255593988 . free .
7. 10.1039/C2CC32656F . Metallodynameric membranes – toward the constitutional transport of gases . G. . Nasr . T. . Macron . A. . Gilles . Z. . Mouline . M. . Barboiu . Chemical Communications . 2012 . 48 . 54 . 6827–6829. 22652555 .